(R)-3,4-bis(benzyloxy)-5-((S)-1-hydroxy-2-(trityloxy)ethyl)furan-2(5H)-one | 1150100-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (R)-3,4-bis(benzyloxy)-5-((S)-1-hydroxy-2-(trityloxy)ethyl)furan-2(5H)-one
• CAS: 1150100-17-6
• 化学式: C₃₉H₃₄O₆
• 分子量: 598.695
• InChiKey: RJCYTJNNNPZCTR-OIDHKYIRSA-N

物化性质

• 沸点：
  813.7±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  45.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-3,4-bis(benzyloxy)-5-((S)-1-hydroxy-2-(trityloxy)ethyl)furan-2(5H)-one 在 盐酸 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  Design, synthesis and biological evaluation of brain targeting l-ascorbic acid prodrugs of ibuprofen with “lock-in” function

  摘要：

  A novel brain targeting L-ascorbic acid derivatives with "lock-in" function were designed and synthesized as prodrugs to achieve the effective delivery of ibuprofen to brain by glucose transporter 1 (GLUT(1)) and the Na+-dependent vitamin C transporter SVCT2. Ibuprofen-loaded four prodrugs were tested in the animals. Results from the in vivo distribution study after i.v. administration of these four prodrugs and naked ibuprofen indicated that four prodrugs exhibited excellent transport ability across the BBB and significantly increased the level of ibuprofen in brain. Among them, prodrugs 4 showed higher brain concentration. Both biodistribution data and pharmacokinetic parameters suggested that L-ascorbic acid thiamine disulfide delivery system was a promising carrier to enhance CNS drug's delivery ability into brain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.072
• 作为产物：
  描述：

  维生素 C 在 potassium carbonate 、 三乙胺 、 乙酰氯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成 (R)-3,4-bis(benzyloxy)-5-((S)-1-hydroxy-2-(trityloxy)ethyl)furan-2(5H)-one
  参考文献：
  名称：

  Design, synthesis and biological evaluation of brain targeting l-ascorbic acid prodrugs of ibuprofen with “lock-in” function

  摘要：

  A novel brain targeting L-ascorbic acid derivatives with "lock-in" function were designed and synthesized as prodrugs to achieve the effective delivery of ibuprofen to brain by glucose transporter 1 (GLUT(1)) and the Na+-dependent vitamin C transporter SVCT2. Ibuprofen-loaded four prodrugs were tested in the animals. Results from the in vivo distribution study after i.v. administration of these four prodrugs and naked ibuprofen indicated that four prodrugs exhibited excellent transport ability across the BBB and significantly increased the level of ibuprofen in brain. Among them, prodrugs 4 showed higher brain concentration. Both biodistribution data and pharmacokinetic parameters suggested that L-ascorbic acid thiamine disulfide delivery system was a promising carrier to enhance CNS drug's delivery ability into brain. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.072

文献信息

• 10.3998/ark.5550190.p009.781
  作者：Tanini, Damiano、Gori, Marianna、Bicocchi, Francesco、Ambrosi, Moira、Nostro, Pierandrea Lo、Capperucci, Antonella

  DOI：10.3998/ark.5550190.p009.781

  日期：——
• Design, synthesis and preliminary biological evaluation of brain targeting l-ascorbic acid prodrugs of ibuprofen
  作者：Xue-Ying Wu、Xiao-Cen Li、Jie Mi、Jing You、Li Hai

  DOI：10.1016/j.cclet.2013.01.022

  日期：2013.2

  L-Ascorbic acid (AA, vitamin C) exhibits a high concentration in the brain. The transportation of AA in brain is mainly mediated by the glucose transporter 1 (GLUT(1)) and the Ne-dependent vitamin C transporter SVCT2. While L-ascorbic acid C6-O conjugation has been investigated as a tool to enhance brain drug delivery, C5-O conjugation and C5-O & C6-O conjugation as brain targeting tools have not been reported. In this letter, ibuprofen was linked directly to C5-O, C6-O and C5-O 82 C6-O positions of ',ascorbic acid with eater bonds, providing prodrug 1, 2 and 3, respectively, to improve their targeting abilities in the brain. Prodrug 1, 2 and 3 were synthesized in facile ways with good yields. And the preliminary evaluation in vivo illustrated that prodrug 2 had a better targeting ability than prodrug I. Moreover, prodrug 3, whose C5-O & C6-O positions were both modified, had good targeting ability for brain which will provide an important evidence for our further study on C5-O & C6-O- di-derivatives of L-ascorbic acid. (C) 2013 Li Hai. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Design and efficient synthesis of novel ascorbyl conjugated peptide with high collagen biosynthesis stimulating effects
  作者：Ho-Il Choi、Heung-Jae Kim、Jong-Il Park、Eun-Ho Shin、Dong-Won Kim、Soung-Soo Kim

  DOI：10.1016/j.bmcl.2008.10.112

  日期：2009.4

  Collagen is critical for skin strength and elasticity, and its degradation leads to wrinkles that accompany aging. Based emphasis on the aesthetics, we tried to make a new compound that can highly stimulate collagen biosynthesis and synthesized ascorbyl conjugated peptide that is a complex form connected by succinoyl linker. We conducted several in vitro and in vivo experiments to identify if the compound has a potent activity, comparing to the ascorbic acid only for collagen biosynthesis. Our in vitro and in vivo result identified that ascorbyl conjugated peptide can stimulate collagen biosynthesis in human dermis and is assumably stable in the rat skin extracts. In conclusion, we strongly suggest that ascorbyl conjugated peptide can be used as a main ingredient for cosmetic products as well as wound healing agents. (C) 2008 Elsevier Ltd. All rights reserved.